US4055639A - Derivatives of N-(2,2-dichlorovinyl) salicylamide and use thereof as bactericides, fungicides and algicides for industry - Google Patents
Derivatives of N-(2,2-dichlorovinyl) salicylamide and use thereof as bactericides, fungicides and algicides for industry Download PDFInfo
- Publication number
- US4055639A US4055639A US05/595,748 US59574875A US4055639A US 4055639 A US4055639 A US 4055639A US 59574875 A US59574875 A US 59574875A US 4055639 A US4055639 A US 4055639A
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- United States
- Prior art keywords
- atom
- group
- valence
- hydrogen atom
- chlorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 12
- LVGMAMQRLHNOCL-UHFFFAOYSA-N n-(2,2-dichloroethenyl)-2-hydroxybenzamide Chemical class OC1=CC=CC=C1C(=O)NC=C(Cl)Cl LVGMAMQRLHNOCL-UHFFFAOYSA-N 0.000 title description 5
- 239000003619 algicide Substances 0.000 title 1
- 239000003899 bactericide agent Substances 0.000 title 1
- 239000000417 fungicide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 125000004429 atom Chemical group 0.000 claims abstract description 35
- 229910052751 metal Chemical group 0.000 claims abstract description 34
- 239000002184 metal Chemical group 0.000 claims abstract description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 31
- 241000894006 Bacteria Species 0.000 claims abstract description 28
- 241000233866 Fungi Species 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
- 241000195493 Cryptophyta Species 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 14
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 230000002353 algacidal effect Effects 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 125000004436 sodium atom Chemical group 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 241001606091 Neophasia menapia Species 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000004550 soluble concentrate Substances 0.000 description 9
- 229960000581 salicylamide Drugs 0.000 description 8
- VCIAQXHGZYZOMU-UHFFFAOYSA-N 5-chloro-n-(2,2-dichloroethenyl)-2-hydroxybenzamide Chemical class OC1=CC=C(Cl)C=C1C(=O)NC=C(Cl)Cl VCIAQXHGZYZOMU-UHFFFAOYSA-N 0.000 description 7
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- -1 wooden articles Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000009036 growth inhibition Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000195628 Chlorophyta Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241001478240 Coccus Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000000622 irritating effect Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000000644 propagated effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- GJCODQOVXZGCGC-UHFFFAOYSA-N 5-chloro-2-hydroxy-n-(2,2,2-trichloro-1-hydroxyethyl)benzamide Chemical compound ClC(Cl)(Cl)C(O)NC(=O)C1=CC(Cl)=CC=C1O GJCODQOVXZGCGC-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241000221955 Chaetomium Species 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000228153 Penicillium citrinum Species 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 244000292604 Salvia columbariae Species 0.000 description 1
- 235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000014167 chia Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Definitions
- the present invention relates to new derivatives of N-(2,2-dichlorovinyl)salicylamide and use thereof for controlling bacteria, fungi and algae which propagate on industrial raw materials, industrial products and in water in circulating water systems.
- the bacteria and fungi on industrial raw materials and products degrade the quality of industrial raw materials and products and cause various other troubles. The damage is very serious.
- the algae which propagate on the bottom of ships cause the slowdown of speed of ships.
- Bacteria, fungi and algae in water in circulating water systems produce mats of slime which restrict the flow of water and reduce the efficiency of heat exchange. They constitute a considerable problem.
- Many compounds having bactericidal, fungicidal and algicidal activity are used for prevention of the damage caused by the bacteria, fungi or algae to industrial raw materials and products and the impediment caused by slime in circulating water systems.
- These compounds include, for example, organic mercury compouds, organic tin compounds, phenols having substituted halogen atoms, organic sulfur compounds, formalin, cresol and quaternary ammonium salts.
- These compounds however, have various defects, for example, strong toxicity against humans and live-stock, pollution of environment, irritative or offensive odor, bad influence upon industrial raw materials and products and weak bactericidal, fungicidal activity.
- the object of the present invention to provide new compounds having bactericidal, fungicidal and algicidal activity against bacteria, fungi and algae which propagate on industrial raw materials and products and in water in circulating water systems, to provide methods for controlling such bacteria, fungi and algae and to provide compositions used for the methods.
- the compounds of the present invention are represented by the formula: ##STR2## wherein X represents hydrogen atom, chlorine atom, bromine atom, methyl group or nitro group, Y represents hydrogen atom, methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 12 carbon atoms and may be substituted by one or more halogen atoms, a lower alkoxy carbonyl group, a lower alkylamino carbonyl group or a metal atom of which the valence is 1 or 2, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y represents said group or said atom except a metal atom of which valence is 2, but when X and Z represent hydrogen atom, Y does not represent hydrogen atom or a metal atom.
- the methods of the present invention comprise applying to industrial raw materials, industrial products and water in circulating water systems an effective amount of one or more compounds of formula (1).
- the bactericidal, fungicidal and algicidal compositions of the present invention comprise 99.5-5% by weight of a suitable adjuvant and 0.5-95% by weight of one or more compounds of formula (1).
- the industrial raw materials and products include organic matter: for example, cellulosic material such as wood, wooden articles, paper, cotton, fibers, textiles and bamboo, petroleum products such as plastics, plastic articles, oils and paints and leathers; inorganic matter such as metal articles; and products consisting of organic and inorganic matter such as ships and sheds for animals.
- cellulosic material such as wood, wooden articles, paper, cotton, fibers, textiles and bamboo
- petroleum products such as plastics, plastic articles, oils and paints and leathers
- inorganic matter such as metal articles
- products consisting of organic and inorganic matter such as ships and sheds for animals.
- circular water systems means a system in which water is used many times by cycling.
- circulating water systems include, for example, the water systems in cooling towers for air conditioning, swimming pools, cooling equipments for reactors and the paper manufacturing industry.
- Suitable adjuvants of the composition of the present invention include, for example, carriers, extenders, emulsifying agents, wetting agents, fixing agents and surface active agents.
- carrier is used herein to mean a diluent or vehicle by which the active compound is brought into contact with bacteria, fungi and algae.
- Solid carrier materials and liquid carrier materials are usually used as carriers in the present invention.
- Solid carrier materials include, for example, clay, kaolin, talc, diatomaceous-earth, silica and calcium carbonate.
- Liquid carrier materials include, for example, benzene, alcohol, acetone, xylene, methylnaphthalene, cyclohexanone, dimethylformamide, diethylsulfoxide, animal and vegetable oils, fatty acids and ester thereof and various surface active agents.
- the compounds of the present invention have superior bactericidal, fungicidal and algicidal activity against bacteria, fungi and algae which propagate on industrial raw materials and industrial products and in water in circulating water systems and have no irritative or offensive odor and very low toxicity.
- the value of acute oral toxicity of the compound of the present invention against as mouse, which is represented by LD 50 is more than 1000 mg/kg. Accordingly, the compounds are safe to handle. Therefore, the compounds are used for controlling said bacteria, fungi and algae.
- the preferred compounds are the compounds of formula (1) in which X represents hydrogen atom, chlorine atom, bromine atom or methyl group, Y represents methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 3 carbon atoms and may be substituted by one or two chlorine atoms, a lower alkoxy carbonyl group where the lower alkoxy group has from 1 to 4 carbon atoms, methylamino carbonyl group, sodium atom, potassium atom, zinc atom or manganese atom, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y represents said group or said atom except a metal atom of which valence is 2.
- the most preferred compounds are the compounds of the formula (1) in which X represents hydrogen atom or chlorine atom, Y represents sodium atom, methylcarbonyl group, ethylcarbonyl group or methoxy carbonyl group and n represents 1.
- These compounds are, for example, sodium salts of N-(2',2'-dichlorovinyl)-5-chlorosalicylamide, O-acetyl-N-(2',2'-dichlorovinyl)-5-chlorosalicylamide, O-acetyl-N-(2',2'-dichlorovinyl) salicylamide and)-ethylcarbonyl-N-(2,2-dichlorovinyl)-salicylamide.
- These compounds are reduced with a reductant such as zinc in a suitable solvent such as acetic acid, methanol or ethanol at a temperature between room temperature and 120° C.
- a reductant such as zinc
- a suitable solvent such as acetic acid, methanol or ethanol
- the alkyl halide is, for example, methyl iodide, ethyl iodide or propyl chlorine.
- the acyl chloride where alkyl group may be substituted halogen atoms is, for example, acetyl chloride, chloroacetylchloride, dichloroacetyl chloride, propionyl chloride, butyryl chloride, isobutyryl chloride or lauroyl chloride.
- the alkoxy carbonyl chloride is, for example, methyl chloroformate, ethyl chloroformate or propyl chloroformate.
- the alkyl isocyanate is, for example, methyl isocyanate or propyl isocyanate.
- the alkali metal hydroxide is, for example, sodium hydroxide or potassium hydroxide.
- the compound of the formula (IV) is reacted with equivalent of a metal halide except alkali metal halide, a metal acetate or a metal sulfate in the presence of alkali metal hydroxide such as sodium hydroxide or potassium hydroxide in water at room temperature to obtain the formula ##STR8## wherein Y" represents metal atom except alkali metal atom and n represents 1 or 2.
- the metal halide is, for example, zinc chloride or manganous chloride.
- the metal acetate is, for example, zinc acetate or copper (II) acetate.
- the metal sulfate is, for example, copper sulfate.
- the compounds are applied to industrial raw materials, industrial products and said water.
- the compounds themselves, may be directly applied to said materials, products and water. However, in general, one or more of the compounds are mixed with suitable adjuvants and formed into bactericidal fungicidal and algicidal compositions such as emulsifiable concentrate, wettable powder, water soluble concentrate, oil soluble concentrate, dust, granules or pellets.
- suitable adjuvants such as emulsifiable concentrate, wettable powder, water soluble concentrate, oil soluble concentrate, dust, granules or pellets.
- the bactericidal, fungicidal and algicidal composition which contains the compounds of the present invention comprises about 0.5 to 95, preferably, 2 to 70 weight percent of the compounds and about 99.5 to 5, preferably 98 to 30 weight percent of suitable adjuvants.
- the compound in the form of a composition is added to them and mixed.
- the amount of the compound added is usually about 0.01 to 0.1 percent by weight.
- the growth of bacteria, fungi and algae on the bottom of ships can be prevented by coating the bottom with the paint containing the compound.
- the active compound is added to the water and the amount of the active compound is usually about 2 to 50 ppm, preferably about 10 to 30 ppm.
- reaction mixture was condenced under the reduced pressure to obtain a solid matter.
- the solid matter was recrystallized from cyclohexane.
- An emulsifiable concentrate containing compound No. 2, No. 5, No. 8, No. 10, No. 13, No. 15, No. 16, No. 19, No. 22 or No. 23 was prepared by the same method as mentioned above.
- a wettable powder was prepared as follows:
- the above ingredients were blended. A wettable powder was obtained. Before application, the wettable powder was suspended in water. The resultant suspension was sprayed on the inside of sheds for animals by a sprayer to prevent the growth of fungi and bacteria in sheds for animals.
- a water soluble concentrate was prepared as follows:
- a water soluble concentrate was obtained.
- a water soluble concentrate containing Compound No. 1, No. 2, No. 5, No. 8, No. 16, No. 19 or No. 22 was prepared by the same method as mentioned above.
- the concentrate was diluted 500-1000 times with water and sprayed on the inside of cotes to prevent the growth of bacteria and fungi.
- the solution was added to water in circular water systems to inhibit the growth of slime.
- the concentration of Compound No. 6 in the water was 10-20 ppm.
- Bactericidal activity and fungicidal activity of the active compounds of the present invention were examined by [1] potato-dextrose agar dilution method, or [2] glucose bouillon medium dilution method. The results are shown in Table 2 below as the minimum inhibitory concentration (the minimum concentration of active compound found to produce 100% control of the test bacteria and fungi).
- the emulsifiable concentrates which were prepared by Example 8 were diluted with water 400 times and 800 times to form emulstions.
- the square plates of beach of which a side was 5 cm long and thickness was 5 mm were dipped into the emulsion for 2 minutes and dried for 24 hours at room temperature.
- the square plates were placed on the surface of agar plates.
- the suspensions which contained spores of Aspergillus niger, Penicillium citrinum, Cladosporium harbarum and chaetomium globusum were respectively sprayed on the agar plates and the square plates.
- test fungi were cultivated in the incubator at the humidity of 95% and the temperature of 28° C for 2 weeks.
- the emulsifiable concentrates which were prepared by Example 8 were diluted with water 100 times to form an emulsion.
- Zero point zero two (0.02) part of active compounds in the form of 10% water soluble concentrate which was prepared by Example 11 was added into 100 parts of Waxman's liquid medium.
- Pieces of wood and iron hereafter referred to as the slime test boards
- the bacteria which were gathered from circular water system were inoculated upon the Waxman's liquid medim and incubated at 27°-34° C by shaking culture for 2 days. The degree of propagation of the bacteria on the slime test boards was examined.
- the growth-inhibiting activity of active compounds against the fungi and the green algae was also examined by the same method as mentioned above.
- the degree of propagation of the bacteria, fungi or green algae on the slime test boards is difined in term of the following symbols.
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Abstract
A new compound represented by the formula ##STR1## WHEREIN X represents hydrogen atom, chlorine atom, bromine atom, methyl group or nitro group, Y represents hydrogen atom, methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 12 carbon atoms and may be substituted by one or more halogen atoms, a lower alkoxy carbonyl group, a lower alkylamino carbonyl group or a metal atom of which the valence is 1 or 2, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y represents said group or said atom except a metal atom of which valence is 2 but when X and Z represent hydrogen atom, Y does not represent hydrogen atom or a metal atom is employed to control the growth of bacteria, fungi and algae which propagate on industrial raw materials and products or in water in circulating water systems.
Description
The present invention relates to new derivatives of N-(2,2-dichlorovinyl)salicylamide and use thereof for controlling bacteria, fungi and algae which propagate on industrial raw materials, industrial products and in water in circulating water systems.
The bacteria and fungi on industrial raw materials and products degrade the quality of industrial raw materials and products and cause various other troubles. The damage is very serious. The algae which propagate on the bottom of ships cause the slowdown of speed of ships.
Bacteria, fungi and algae in water in circulating water systems produce mats of slime which restrict the flow of water and reduce the efficiency of heat exchange. They constitute a considerable problem.
Many compounds having bactericidal, fungicidal and algicidal activity are used for prevention of the damage caused by the bacteria, fungi or algae to industrial raw materials and products and the impediment caused by slime in circulating water systems. These compounds include, for example, organic mercury compouds, organic tin compounds, phenols having substituted halogen atoms, organic sulfur compounds, formalin, cresol and quaternary ammonium salts. These compounds, however, have various defects, for example, strong toxicity against humans and live-stock, pollution of environment, irritative or offensive odor, bad influence upon industrial raw materials and products and weak bactericidal, fungicidal activity.
It is, therefore, the object of the present invention to provide new compounds having bactericidal, fungicidal and algicidal activity against bacteria, fungi and algae which propagate on industrial raw materials and products and in water in circulating water systems, to provide methods for controlling such bacteria, fungi and algae and to provide compositions used for the methods.
The compounds of the present invention are represented by the formula: ##STR2## wherein X represents hydrogen atom, chlorine atom, bromine atom, methyl group or nitro group, Y represents hydrogen atom, methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 12 carbon atoms and may be substituted by one or more halogen atoms, a lower alkoxy carbonyl group, a lower alkylamino carbonyl group or a metal atom of which the valence is 1 or 2, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y represents said group or said atom except a metal atom of which valence is 2, but when X and Z represent hydrogen atom, Y does not represent hydrogen atom or a metal atom.
The methods of the present invention comprise applying to industrial raw materials, industrial products and water in circulating water systems an effective amount of one or more compounds of formula (1).
The bactericidal, fungicidal and algicidal compositions of the present invention comprise 99.5-5% by weight of a suitable adjuvant and 0.5-95% by weight of one or more compounds of formula (1).
The industrial raw materials and products include organic matter: for example, cellulosic material such as wood, wooden articles, paper, cotton, fibers, textiles and bamboo, petroleum products such as plastics, plastic articles, oils and paints and leathers; inorganic matter such as metal articles; and products consisting of organic and inorganic matter such as ships and sheds for animals.
The term "circular water systems" means a system in which water is used many times by cycling. Such circulating water systems include, for example, the water systems in cooling towers for air conditioning, swimming pools, cooling equipments for reactors and the paper manufacturing industry.
Suitable adjuvants of the composition of the present invention include, for example, carriers, extenders, emulsifying agents, wetting agents, fixing agents and surface active agents. The term "carrier" is used herein to mean a diluent or vehicle by which the active compound is brought into contact with bacteria, fungi and algae.
Solid carrier materials and liquid carrier materials are usually used as carriers in the present invention. Solid carrier materials include, for example, clay, kaolin, talc, diatomaceous-earth, silica and calcium carbonate. Liquid carrier materials include, for example, benzene, alcohol, acetone, xylene, methylnaphthalene, cyclohexanone, dimethylformamide, diethylsulfoxide, animal and vegetable oils, fatty acids and ester thereof and various surface active agents.
The compounds of the present invention have superior bactericidal, fungicidal and algicidal activity against bacteria, fungi and algae which propagate on industrial raw materials and industrial products and in water in circulating water systems and have no irritative or offensive odor and very low toxicity. The value of acute oral toxicity of the compound of the present invention against as mouse, which is represented by LD50, is more than 1000 mg/kg. Accordingly, the compounds are safe to handle. Therefore, the compounds are used for controlling said bacteria, fungi and algae.
The preferred compounds are the compounds of formula (1) in which X represents hydrogen atom, chlorine atom, bromine atom or methyl group, Y represents methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 3 carbon atoms and may be substituted by one or two chlorine atoms, a lower alkoxy carbonyl group where the lower alkoxy group has from 1 to 4 carbon atoms, methylamino carbonyl group, sodium atom, potassium atom, zinc atom or manganese atom, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y represents said group or said atom except a metal atom of which valence is 2. The most preferred compounds are the compounds of the formula (1) in which X represents hydrogen atom or chlorine atom, Y represents sodium atom, methylcarbonyl group, ethylcarbonyl group or methoxy carbonyl group and n represents 1. These compounds are, for example, sodium salts of N-(2',2'-dichlorovinyl)-5-chlorosalicylamide, O-acetyl-N-(2',2'-dichlorovinyl)-5-chlorosalicylamide, O-acetyl-N-(2',2'-dichlorovinyl) salicylamide and)-ethylcarbonyl-N-(2,2-dichlorovinyl)-salicylamide.
The compounds of the formula (1) of the present invention are prepared as follows:
The compound of the formula ##STR3## wherein X and Z are defined as above are condensed with chloral by a method similar to that shown in U.S. Pat. No. 2,936,323. The products of the condensation are compounds of the formula ##STR4##
These compounds are reduced with a reductant such as zinc in a suitable solvent such as acetic acid, methanol or ethanol at a temperature between room temperature and 120° C.
Compounds of the formula ##STR5## are obtained by the said reduction. The compound of the formula (IV) is reacted with equivalent mole to 2 times mole of an alkyl halide, an acyl chloride, an alkoxycarbonyl chloride or an alkyl isocyanate in the presence of a suitable base such as trimethylamine and triethylamine in an inactive solvent at a temperature of 5° to 120° C to obtain the compound ##STR6## wherein Y' represents methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 12 carbon atoms and may be substituted by one or more halogen atoms, a lower alkoxy carbonyl group, a lower alkyl amino carbonyl group, and X and Z are defined as above.
The alkyl halide is, for example, methyl iodide, ethyl iodide or propyl chlorine. The acyl chloride where alkyl group may be substituted halogen atoms is, for example, acetyl chloride, chloroacetylchloride, dichloroacetyl chloride, propionyl chloride, butyryl chloride, isobutyryl chloride or lauroyl chloride. The alkoxy carbonyl chloride is, for example, methyl chloroformate, ethyl chloroformate or propyl chloroformate. The alkyl isocyanate is, for example, methyl isocyanate or propyl isocyanate.
The compound of the formula (IV) is reacted with equivalent of an alkali metal hydroxide in water at room temperature to obtain the formula ##STR7## wherein Y" represents alkali metal such as sodium atom or potassium atom.
The alkali metal hydroxide is, for example, sodium hydroxide or potassium hydroxide.
The compound of the formula (IV) is reacted with equivalent of a metal halide except alkali metal halide, a metal acetate or a metal sulfate in the presence of alkali metal hydroxide such as sodium hydroxide or potassium hydroxide in water at room temperature to obtain the formula ##STR8## wherein Y" represents metal atom except alkali metal atom and n represents 1 or 2.
The metal halide is, for example, zinc chloride or manganous chloride. The metal acetate is, for example, zinc acetate or copper (II) acetate. The metal sulfate is, for example, copper sulfate.
In order to control the growth of said bacteria, fungi and algae with the compounds of the present invention, the compounds are applied to industrial raw materials, industrial products and said water.
The compounds, themselves, may be directly applied to said materials, products and water. However, in general, one or more of the compounds are mixed with suitable adjuvants and formed into bactericidal fungicidal and algicidal compositions such as emulsifiable concentrate, wettable powder, water soluble concentrate, oil soluble concentrate, dust, granules or pellets.
The bactericidal, fungicidal and algicidal composition which contains the compounds of the present invention comprises about 0.5 to 95, preferably, 2 to 70 weight percent of the compounds and about 99.5 to 5, preferably 98 to 30 weight percent of suitable adjuvants.
In the case of treatment of industrial raw materials or products such as wood, wooden articles, fibers, textiles, paper, leathers, inside of sheds for animals, etc., usually their surfaces are treated with 0.1-10 g/m2 of the compound in the form of a composition by means of spraying, coating or infiltrating.
In the case of treatment of industrial raw materials or products such as paints, adhesives and pastes, etc., usually the compound in the form of a composition is added to them and mixed. The amount of the compound added is usually about 0.01 to 0.1 percent by weight.
The growth of bacteria, fungi and algae on the bottom of ships can be prevented by coating the bottom with the paint containing the compound.
In the case of treatment of water in circulating water systems, the active compound is added to the water and the amount of the active compound is usually about 2 to 50 ppm, preferably about 10 to 30 ppm.
Thirty (30) g (0.09 mol) of N-(1'-hydroxy-2',2',2'-trichloroethyl)-5-chlorosalicylamide were dissolved in 150 ml of acetic acid. Nine point two (9.2) g (0.14 mol) of zinc powder were added into the solution under stirring at the temperature from 20° to 40° C and the reaction was continued for 4 hours at the same temperature. The temperature was finally raised at 80° C and then excess zinc was removed by filtration. The filtrate was cooled to obtain 28 g of crystals of N-(2',2'-dichlorovinyl)-5-chlorosalicylamide was obtained. Melting point of it was 208°-210° C.
Elemental analysis for C9 H6 Cl3 NO2 :
Calculation: C, 40.56%; H, 2.27%; N, 5.26%. Found: C, 40.37%; H, 2.23%; N, 5.65%.
One hundred and fifty (150) g (0.65 mol) of N-(2,2-dichlorovinyl) salicylamide was suspended into 450 ml of benzene. Two hundred (200) g (1.95 mol) of acetic anhydride was added into the suspension with stirring. After 10 g (0.13 mol) of pyridine was added dropwise to the solution at 30°-40° C, the mixture was refluxed for 5 hours. After cooling, the reaction mixture was washed with water and an aqueous solution of 5%-sodium hydrogen-carbonate, and again with water.
Then the reaction mixture was condenced under the reduced pressure to obtain a solid matter. The solid matter was recrystallized from cyclohexane. One hundred and seventy (170) g of O-acetyl-N-(2,2-dichlorovinyl) salicylamide, m.p. 91°-92° C, was obtained.
Elemental analysis for C11 H9 Cl2 NO3 : Calculation: C, 48.20%; H, 3.31%; N, 5.11%. Found: C, 48.30%; H, 3.06%; N, 5.08%.
Twenty (20) g (0.09 mol) of N-(2,2-dichlorovinyl) salicylamide were dissolved into 100 ml of benzene. Eight point one (8.1) g (0.09 mol) of methyl chloroformate were added to the solution with stirring. After 9 g (0.09 mol) of triethylamine were added dropwise under 10° C the mixture was reacted for 3 hours at the room temperature and refluxed for 30 minutes to complete the reaction. After cooling, the reaction mixture was washed with water, an aqueous solution of 5%-sodium hydrogencarbonate, and finally with water to obtain the neutral reaction mixture. The neutral reaction mixture was concentrated under reduced pressure to obtain a solid matter. The solid matter was recrystallized from methanol. Twenty two point five (22.5) g of O-(N'-methoxy carbamoyl)-N-(2,2-dichlorovinyl) salicylamide, m.p. 72°-73° C, was obtained.
Elemental analysis for C11 H9 Cl2 NO4 :
Calculation: C, 45.54%; H, 3.13%; N, 4.83%. Found: C, 45.30%; H, 3.10%; N, 4.61%.
Twelve (12) g (0.05 mol) of N-(2,2-dichlorovinyl) salicylamide were dissolved in 100 ml of benzene and 4 g (0.07 mol) of methyl isocyanate were added with stirring at below 10° C. Six point six (6.6) g (0.07 mol) of triethylamine were added dropwise to the solution. The mixture was reacted for 3 hours at room temperature and refluxed for 30 minutes. The reaction mixture was cooled and washed with water, then an aqueous solution of 5%-sodium hydrocarbonate and finally water to obtain the neutral reaction mixture. The neutral reaction mixture was concentrated to obtain a solid matter under the reduced pressure. The solid matter was recrystallized from methanol. Thirteen point five (13.5) g of O-(N'-methylcarbamoyl)-N-(2,2-dichlorovinyl) salicylamide (m.p. 98°-101° C) were obtained.
Elemental analysis for C11 H10 Cl2 N2 O3 : Calculated: C, 45.70%; H, 3.49%; N, 9.69%. Found: C, 45.81%; H, 3.45%; N, 9.60%.
Five (5) g (0.018 mol) of N-(2',2'-dichlorovinyl)-5-chlorosalicylamide were dissolved in 30 ml of benzene, and 2.2 g (0.022 mol) of acetic anhydride and a few drops of pyridine were added with stirring. The mixture was stirred for 4 hours at 50° C. The reaction mixture was washed with water, an aqueous solution of 5%-sodium hydrocarbonate and water, successively. The reaction mixture was concentrated under the reduced pressure to obtain a solid matter. The solid matter was recrystallized from benzene. Four (4) g of O-acetyl-N-(2',2'-dichlorovinyl)-5-chlorosalicylamide, m.p. 98°-100° C, were obtained.
Elemental anarysis for C11 H7 Cl3 NO3 : Calculation: C, 42.82%; H, 2.61%; N, 4.54%. Found: C, 42.65%; H, 2.70%; N, 4.41%.
Five (5) g (0.019 mol) of N-(2',2'-dichlorovinyl)-5-chlorosalicylamide were added under agitation to the aqueous solution wherein 0.7 g (0.019 mol) of 93%-sodium hydroxide were dissolved in 30 ml of water and then agitated at room temperature for 1 hour.
Water was evaporated under reduced pressure. The yields of sodium salt of N-(2',2'-dichlorovinyl)-5-chlorosalicylamide was 5.4. The sodium salt was pale light brown crystals and melting point of it was over 280° C.
Elemental analysis as C9 H5 Cl3 NO2 Na5 : Calculated: C, 37.47%; H, 1.75%; N, 4.86%. Found: C, 37.33%; H, 1.73%; N, 4.79%.
The compounds shown in Table 1 were prepared.
Table 1 __________________________________________________________________________ ##STR9## Com- X and M.P. A material com- pound position (° C) Method of pound corres- No. of Y Z n or n.sub.D.sup.25 Appearance the preparation ponding to Y __________________________________________________________________________ group 7 5-Br Na H 1 Over Pale brown Similar method NaOH 280 crystals to Example 6 N-(2',2'-dichloro- vinyl)-5-bromo- salicylamido was 8 5-Br Zn H 2 " White reacted with crystals equivalent of ZnCl.sub.2 Zncl.sub.2 in the presence of NaOH in water at room temperature. Dark Similar method 9 5-Br Cu (II) H 2 " yellow to the prepara- CuSO.sub.4 green tion of compo- crystals und No. 8 Yellow 10 5-Br Mu (II) H 2 " grey " MnCl.sub.2 crystals 11 4-CH.sub.3 H H 1 m.p. White Similar method 189-191 crystals to Example 1 12 3-CH.sub.3 H H 1 m.p. White " 78-82 crystals 13 5-Br H H 1 m.p. 204 White " crystals Nitration of N- (2,2-dichloro- vinyl) salicyl- Pale amide with 14 3-NO.sub.2 H H 1 m.p. yellow equivalent mole 176-177 crystals of nitric acid in the presence of acetic acid at room tempera- ture. 15 H C(O)C.sub.2 H.sub.5 H 1 m.p. White Similar method ClC(O)C.sub.2 H.sub.5 37-38 crystals to Example 2 16 H C(O)C.sub.3 H.sub.7 (n) H 1 m.p. White " ClC(O)C.sub.3 H.sub.7 (n) 124-125 crystals 17 H C(O)C.sub.3 H.sub.7 (i) H 1 m.p. White " ClC(O)C.sub.3 H.sub.7 (i) 122-124 crystals 18 H C(O)C.sub.11 H.sub.23 (n) H 1 m.p. White " ClC(O)C.sub.11 H.sub.23 (n) 53-59 crystals 19 H C(O)CH.sub.2 Cl H 1 m.p. White Similar method ClC(O)CH.sub.2 Cl 93-95 crystals to Example 2 20 H C(O)CHCl.sub.2 H 1 m.p. White " ClC(O)CHCl.sub.2 184-186 crystals 21 5-Br C(O)CH.sub.3 H 1 m.p. White Similar method ClC(O)CH.sub.3 133-134 crystals to Example 5 22 H C(O)OC.sub.2 H.sub.5 H 1 m.p. White Similar method ClCOOC.sub.2 H.sub.5 70-72 crystals to Example 3 23 H ##STR10## H 1 n.sub.D.sup.25 1.5409 Transparet liquid " ##STR11## Alkylation of N- (2,2-dichloro- 24 H CH.sub.3 H 1 m.p. White vinyl) salicyl- CH.sub.3 I 111-112 crystals amide with methyl iodide Pale 25 5-Cl K H 1 m.p. Yellow Similar method KOH over 280 crystals to Example 6 26 3-Cl H 5-Cl 1 m.p. White Similar method 173.5- crystals to Example 1 174.0 27 3-Cl C(O)CH.sub.3 5-Cl 1 m.p. White Similar method ClC(O)CH.sub.3 130-132 crystals to Example 5 Pale 28 3-Cl Na 5-Cl 1 m.p. yellow Similar method NaOH over 280 crystals to Example 6 Pale 29 3-Cl K 5-Cl 1 m.p. yellow " KOH over 280 crystals Pale 30 3-NO.sub.2 C(O)CH.sub.3 H 1 m.p. yellow Similar method ClC(O)CH.sub.3 109-112 crystals to Example 5 __________________________________________________________________________
An emulsifiable concentrate was prepared as follows:
Compound No. 1: 10 parts
Isophorone: 40 parts
Xylene: 31 parts
Dimethylformamide: 7 parts
Surface active agents: 12 parts
The above ingredients were blended. An emulsifiable concentrate was obtained. Before application, the emulsifiable concentrate was diluted with water up to 400-2000 times and an emulsion was formed. Woods and fibers were soaked in the emulsion to control bacteria and fungi which propagate on them.
An emulsifiable concentrate containing compound No. 2, No. 5, No. 8, No. 10, No. 13, No. 15, No. 16, No. 19, No. 22 or No. 23 was prepared by the same method as mentioned above.
An oil soluble concentrate was prepared as follows:
Compound No. 15: 20 parts
Ethyl cellosolve: 40 parts
Dimethylformamide: 10 parts
Xylene: 30 parts
The above ingredients were mixed. An oil soluble concentrate was obtained. In the form of the oil soluble concentrate, Compound No. 15 was added to paints or the cutting oil in an amount of 0.1%.
A wettable powder was prepared as follows:
Compound No. 5: 55 parts
Polyethyleneoxide: 3 parts
Ligninsulfonic acid: 5 parts
Diatom earth: 20 parts
Clay: 17 parts
The above ingredients were blended. A wettable powder was obtained. Before application, the wettable powder was suspended in water. The resultant suspension was sprayed on the inside of sheds for animals by a sprayer to prevent the growth of fungi and bacteria in sheds for animals.
A water soluble concentrate was prepared as follows:
Compound No. 6: 10 parts
Ethyl cellosolve: 40 parts
Isophoron: 38 parts
Polyethyleneoxide: 10 parts
Alkylbenzenesulfonic acid: 2 parts
The above ingredients were mixed. A water soluble concentrate was obtained. A water soluble concentrate containing Compound No. 1, No. 2, No. 5, No. 8, No. 16, No. 19 or No. 22 was prepared by the same method as mentioned above.
Before application, the concentrate was diluted 500-1000 times with water and sprayed on the inside of cotes to prevent the growth of bacteria and fungi.
The solution was added to water in circular water systems to inhibit the growth of slime. The concentration of Compound No. 6 in the water was 10-20 ppm.
An amount of 0.01-0.1% of Compound No. 6 as the solution was added to pastes or binding agents to prevent rottenness of them. Bacteria, fungi and slime were inhibited for a long time.
Bactericidal activity and fungicidal activity of the active compounds of the present invention were examined by [1] potato-dextrose agar dilution method, or [2] glucose bouillon medium dilution method. The results are shown in Table 2 below as the minimum inhibitory concentration (the minimum concentration of active compound found to produce 100% control of the test bacteria and fungi).
Table 2 __________________________________________________________________________ Minimum inhibitory amount (mcg/ml) Method (1) (2) Bacteria and Fungi Active Asper- Penicil- Clados- Staphylo- Escheri- Compound gillus lium porium Bacillus coccus chia No. niger citrinum harbarum subtilis aureus coli __________________________________________________________________________ 1 10 10 5 5 5 60 2 10 10 5 2.5 5 40 3 10 20 10 10 10 60 4 20 10 5 10 10 60 5 2.5 2.5 2.5 1.3 1.3 10 6 10 5 5 2.5 2.5 40 8 20 20 10 5 5 60 10 20 20 10 5 10 60 12 20 20 20 10 10 80 13 20 10 10 5 5 60 14 10 10 10 5 5 60 15 10 10 5 2.5 5 40 16 10 10 5 5 10 60 17 10 10 10 5 5 40 19 10 10 5 5 5 40 20 10 10 10 5 10 60 22 10 10 10 5 2.5 40 23 10 10 10 5 5 40 24 20 20 10 10 10 60 26 10 10 5 5 5 40 27 10 5 5 2.5 2.5 40 __________________________________________________________________________
The emulsifiable concentrates which were prepared by Example 8 were diluted with water 400 times and 800 times to form emulstions.
The square plates of beach of which a side was 5 cm long and thickness was 5 mm were dipped into the emulsion for 2 minutes and dried for 24 hours at room temperature.
The square plates were placed on the surface of agar plates. The suspensions which contained spores of Aspergillus niger, Penicillium citrinum, Cladosporium harbarum and chaetomium globusum were respectively sprayed on the agar plates and the square plates.
The test fungi were cultivated in the incubator at the humidity of 95% and the temperature of 28° C for 2 weeks.
The results are shown in Table 3. The degree of growth inhibition is defined in term of the following numerical ratings.
Table 3 ______________________________________ Degree of growth inhibition Concentrate of active compound Compound 0.025 % 0.0125 % ______________________________________ 1 3 2 2 3 3 5 5 5 8 3 2 10 3 2 13 3 3 15 3 3 16 3 3 19 3 2 22 3 2 23 3 2 No treatment 1 1 ______________________________________ 3 : 100% control of the test organism. 2 : The part in which the test organisms propagated is less than one thir of the surface of the test plate. 1 : The part in which the test organisms propagated is more than one thir of the surface of the test plate.
The emulsifiable concentrates which were prepared by Example 8 were diluted with water 100 times to form an emulsion.
A cloth of cotton was soaked into each emulsion for 2 minutes. The clothes were dried at room temperature and cut into a square of which a side was 1 cm long. Each kind of test bacteria and fungi was inoculated, separately, on plates of potato-agar and one square cloth was placed on each of such plates. Test bacteria and fungi were cultivated at 28° C for 4 days. The width of the region of growth-inhibition which was formed a circumference of the cloth was measured. The results are shown in Table 4.
Table 4 ______________________________________ The width of the region of growth-inhibition(mm) Fungi Bacteria Aspergil- Penicil- Bacillus Staphylo- Compound lus lium coccus No. niger citrinum subtilis oureus ______________________________________ 1 5 5 9 10 2 5 7 9 7 5 10 10 12 11 8 6 5 6 6 15 6 6 9 7 19 6 7 7 6 22 5 6 8 7 No treated 0 0 0 0 ______________________________________
Zero point zero two (0.02) part of active compounds in the form of 10% water soluble concentrate which was prepared by Example 11 was added into 100 parts of Waxman's liquid medium. Pieces of wood and iron (hereafter referred to as the slime test boards) were soaked into the Waxman's liquid medium. The bacteria which were gathered from circular water system were inoculated upon the Waxman's liquid medim and incubated at 27°-34° C by shaking culture for 2 days. The degree of propagation of the bacteria on the slime test boards was examined.
The growth-inhibiting activity of active compounds against the fungi and the green algae was also examined by the same method as mentioned above.
The results are shown in Table 5.
The degree of propagation of the bacteria, fungi or green algae on the slime test boards is difined in term of the following symbols.
Table 5 ______________________________________ Compound Degree of propagation No. Bacteria Fungi Green algae ______________________________________ 1 - - - 2 - - - 5 - - - 6 - - - 8 + + + 15 - - - 16 + - - 19 - - - 22 - + + No treatment ++++ ++++ ++++ ______________________________________ - : no propagation + : the area of propagation is 1-25% on the slime test boards. ++ : the area of propagation is 26-50% on the slime test boards. +++ : the area of propagation is 51-75% on the slime test boards. ++++ : the area of propagation is 76-100% on the slime test boards.
Claims (9)
1. A compound represented by the formula ##STR12##wherein X represents hydrogen atom, chlorine atom, bromine atom, methyl group or nitro group, Y represents hydrogen atom, methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 12 carbon atoms and may be substituted by one or more halogen atoms, a lower alkoxy carbonyl group, a lower alkylamino carbonyl group or a metal atom of which valence is 1 or 2, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y does not represent a metal atom of which valence is 2, but when X and Z represent hydrogen atom, Y does not represent hydrogen atom or a metal atom.
2. A compound according to claim 1 wherein X represents hydrogen atom, chlorine atom, bromine atom or methyl group, Y represents methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 3 carbon atoms and may be substituted by one or two chlorine atoms, a lower alkoxy carbonyl group where the lower alkoxy group has from 1 to 4 carbon atoms, methylamino carbonyl group, sodium atom, pottassium atom, zinc atom or manganese atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y does not represent a metal atom of which valence is 2.
3. A compound according to claim 2 wherein X represents hydrogen atom or chlorine atom, Y represents sodium atom.
4. A method for killing bacteria, fungi and algae comprising applying to industrial raw materials, industrial products and water in circular water systems an effective amount of one or more compounds of the formula ##STR13## wherein X represents hydrogen atom, chlorine atom, bromine atom, methyl group or nitro group, Y represents hydrogen atom, methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 12 carbon atoms and may be substituted by one or more halogen atoms, a lower alkoxycarbonyl group, a lower alkylamino carbonyl group or a metal atom of which valence is 1 or 2, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y does not represent a metal atom of which valence is 2, but when X and Z represent hydrogen atom, Y does not represent hydrogen atom or a metal atom.
5. A method for killing bacteria, fungi and algae according to claim 4 wherein X represents hydrogen atom, chlorine atom, bromine atom, or methyl group, Y represents methyl group an alkylcarbonyl group where the alkyl group has from 1 to 3 carbon atoms and may be substituted by one or two chlorine atoms, a lower alkoxycarbonyl group where the lower alkoxy group has from 1 to 4 carbon atoms, methylamino carbonyl group, sodium atom, pottassium atom, zinc atom or manganese atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y does not represent a metal atom of which valence is 2.
6. A method for killing bacteria, fungi and algae according to claim 5 wherein X represents hydrogen atom or chlorine atom, Y represents sodium atom, methylcarbonyl group or ethylcarbonyl group and n represents 1.
7. A bactericidal, fungicidal and algicidal composition comprising 99.5-5% by weight of a suitable adjuvant and 0.5-95% by weight of one or more compounds of general formula ##STR14##wherein X represents hydrogen atom, chlorine atom, bromine atom, methyl group or nitro group, Y represents hydrogen atom, methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 12 carbon atoms and may be substituted by one or more halogen atoms, a lower alkoxy carbonyl group, a lower alkylamino carbonyl group or a metal atom of which valence is 1 or 2, Z represents hydrogen atom or chlorine atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y does not represent a metal atom of which valence is 2, but when X and Z represent hydrogen atom, Y does not represent hydrogen atom or a metal atom.
8. A bactericidal, fungicial and algicidal composition according to claim 7 wherein X represents hydrogen atom, chlorine atom, bromine atom or methyl group, Y represents methyl group, an alkylcarbonyl group where the alkyl group has from 1 to 3 carbon atoms and may be substituted by one or two chlorine atoms, a lower alkoxy carbonyl group where the lower alkoxy group has from 1 to 4 carbon atoms, methylamino carbonyl group, sodium atom, pottassium atom, zinc atom or manganese atom and n represents 2 when Y represents a metal atom of which valence is 2 and n represents 1 when Y does not represent a metal atom of which valence is 2.
9. A bactericidal, fungicidal and algicidal composition according to claim 8 wherein Y represents sodium atom, methylcarbonyl group or ethylcarbonyl group and n represents 1.
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/595,748 US4055639A (en) | 1975-07-14 | 1975-07-14 | Derivatives of N-(2,2-dichlorovinyl) salicylamide and use thereof as bactericides, fungicides and algicides for industry |
US05/649,555 US4055640A (en) | 1975-07-14 | 1976-01-15 | Compositions and methods for controlling the growth of bacteria, fungi and algae using certain derivatives of N-(2,2-dichlorovinyl)salicylamides |
GB28470/76A GB1518377A (en) | 1975-07-14 | 1976-07-08 | N-(2,2-dichlorovinyl)salicylamide and its derivatives |
FR7621538A FR2318147A1 (en) | 1975-07-14 | 1976-07-13 | N- (2,2-DICHLOROVINYL) SALICYLAMIDE DERIVATIVES AND THEIR USE AS BACTERICIDES, FUNGICIDES AND ALGICIDES IN INDUSTRY |
CA256,847A CA1077514A (en) | 1975-07-14 | 1976-07-13 | Derivatives of n-(2,2-dichlorovinyl) salicylamide and use thereof as bactericide, fungicide and algicide for industry |
NL7607796A NL7607796A (en) | 1975-07-14 | 1976-07-14 | N- (2.2-DICHLORVINYL) SALICYLAMIDE DERIVATIVES AND THEIR USES AS BACTERICIDE, FUNGICIDE AND ALGICIDE. |
DE19762631710 DE2631710A1 (en) | 1975-07-14 | 1976-07-14 | N- (2 ', 2'-DICHLORAVINYL) SALICYLIC ACID AMIDE AND BIOCIDAL AGENTS CONTAINING THESE COMPOUNDS |
AU21237/77A AU507483B2 (en) | 1975-07-14 | 1977-01-12 | Salicylamides and their use as fungicides and bactericides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/595,748 US4055639A (en) | 1975-07-14 | 1975-07-14 | Derivatives of N-(2,2-dichlorovinyl) salicylamide and use thereof as bactericides, fungicides and algicides for industry |
AU21237/77A AU507483B2 (en) | 1975-07-14 | 1977-01-12 | Salicylamides and their use as fungicides and bactericides |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/649,555 Continuation-In-Part US4055640A (en) | 1975-07-14 | 1976-01-15 | Compositions and methods for controlling the growth of bacteria, fungi and algae using certain derivatives of N-(2,2-dichlorovinyl)salicylamides |
Publications (1)
Publication Number | Publication Date |
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US4055639A true US4055639A (en) | 1977-10-25 |
Family
ID=25618164
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/595,748 Expired - Lifetime US4055639A (en) | 1975-07-14 | 1975-07-14 | Derivatives of N-(2,2-dichlorovinyl) salicylamide and use thereof as bactericides, fungicides and algicides for industry |
Country Status (7)
Country | Link |
---|---|
US (1) | US4055639A (en) |
AU (1) | AU507483B2 (en) |
CA (1) | CA1077514A (en) |
DE (1) | DE2631710A1 (en) |
FR (1) | FR2318147A1 (en) |
GB (1) | GB1518377A (en) |
NL (1) | NL7607796A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4284628A (en) * | 1978-08-25 | 1981-08-18 | Nippon Kayaku Kabushiki Kaisha | 2-Hydroxy benzamide derivatives and use thereof as a fungicide |
US20060005741A1 (en) * | 2003-08-05 | 2006-01-12 | Shunichi Yamazaki | Ship bottom paint additive using coal ash and diatomaceous earth |
US20070048541A1 (en) * | 2005-08-31 | 2007-03-01 | Ou Nian-Hua | Wood panel containing inner culm flakes |
US20070077445A1 (en) * | 2005-09-30 | 2007-04-05 | Lawson Eric N | Panel containing bamboo and fungicide |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5215823A (en) * | 1975-07-18 | 1977-02-05 | Nippon Kayaku Co Ltd | Germicide for agriculture and gardening |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2895992A (en) * | 1959-07-21 | Process for the production of benzoic | ||
US2923737A (en) * | 1960-02-02 | Benzoic acid amides showing antimy- | ||
US2936323A (en) * | 1957-10-16 | 1960-05-10 | Diamond Alkali Co | Chemical composition and process |
-
1975
- 1975-07-14 US US05/595,748 patent/US4055639A/en not_active Expired - Lifetime
-
1976
- 1976-07-08 GB GB28470/76A patent/GB1518377A/en not_active Expired
- 1976-07-13 CA CA256,847A patent/CA1077514A/en not_active Expired
- 1976-07-13 FR FR7621538A patent/FR2318147A1/en not_active Withdrawn
- 1976-07-14 NL NL7607796A patent/NL7607796A/en not_active Application Discontinuation
- 1976-07-14 DE DE19762631710 patent/DE2631710A1/en not_active Withdrawn
-
1977
- 1977-01-12 AU AU21237/77A patent/AU507483B2/en not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2895992A (en) * | 1959-07-21 | Process for the production of benzoic | ||
US2923737A (en) * | 1960-02-02 | Benzoic acid amides showing antimy- | ||
US2936323A (en) * | 1957-10-16 | 1960-05-10 | Diamond Alkali Co | Chemical composition and process |
Non-Patent Citations (2)
Title |
---|
Chemical Abstracts 75:139927z (1971). * |
Chemical Abstracts 78:42611r (1973). * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4284628A (en) * | 1978-08-25 | 1981-08-18 | Nippon Kayaku Kabushiki Kaisha | 2-Hydroxy benzamide derivatives and use thereof as a fungicide |
US20060005741A1 (en) * | 2003-08-05 | 2006-01-12 | Shunichi Yamazaki | Ship bottom paint additive using coal ash and diatomaceous earth |
US7048788B2 (en) * | 2003-08-05 | 2006-05-23 | Shunichi Yamazaki | Ship bottom paint using coal ash and diatomaceous earth |
US20070048541A1 (en) * | 2005-08-31 | 2007-03-01 | Ou Nian-Hua | Wood panel containing inner culm flakes |
US7625631B2 (en) | 2005-08-31 | 2009-12-01 | Huber Engineered Woods Llc | Wood panel containing inner culm flakes |
US20070077445A1 (en) * | 2005-09-30 | 2007-04-05 | Lawson Eric N | Panel containing bamboo and fungicide |
Also Published As
Publication number | Publication date |
---|---|
NL7607796A (en) | 1977-01-18 |
AU2123777A (en) | 1978-07-20 |
GB1518377A (en) | 1978-07-19 |
FR2318147A1 (en) | 1977-02-11 |
DE2631710A1 (en) | 1977-01-20 |
CA1077514A (en) | 1980-05-13 |
AU507483B2 (en) | 1980-02-14 |
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